Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
  • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
  • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D207/36—Oxygen or sulfur atoms
  • C07D207/40—2,5-Pyrrolidine-diones
  • C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
  • C07D207/408—Radicals containing only hydrogen and carbon atoms attached to ring carbon atoms

Definitions

• Certain diphenyl ether ureas are known to be useful as herbicides.
• U.S. Pat. No. 3,119,682 discloses certain mono- and dialkylamino diphenyl ether ureas as suitable herbicides.
• This appliation relates to novel diphenyl ether amides.
• this application relates to novel diphenyl ether amides having the formula ##STR1## in which X is chloro or methyl; n is zero, one or two; Y is chloro or trifluoromethyl; R 1 is hydrogen, alkyl, lower alkoxy, lower haloalkyl, thio-lower alkyl, or alkenyl; R 2 is hydrogen, lower alkoxy-alkyl or lower alkanoyl; or R 1 and R 2 taken together is ##STR2##
• alkyl is meant aliphatic radicals, both straight chain and branched chain, generally those having from 1 to about 10 carbon atoms, preferably from 1 to about 6 carbon atoms, for example, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, t-butyl, n-amyl, is
• lower alkoxy By the terms “lower alkoxy”, “thio-lower alkyl”, “lower haloalkyl”, “lower alkoxy-alkyl”, and “lower alkanoyl” are meant such groups containing from 1 to about 4 carbon atoms, for example, methoxy, ethoxy, propoxy, butoxy, thio-methyl, thio-ethyl, chloromethyl, dichloromethyl, trichloromethyl, trifluoromethyl, methoxymethyl, ethoxyethyl, ethoxymethyl, formyl, acetyl, propionyl, butyryl, isobutyryl, and the like.
• alkenyl is meant an olefinic group having at least one olefinic bond and having from 2 to about 5 carbon atoms, for example, vinyl, allyl, propenyl, butenyl and the like.
• the compounds of this invention have been found to be active herbicides, that is, certain members of the class have been found to be herbicidally effective against a wide range of plant species. More particularly, the compounds of the present invention are characterized by having little or no pre-emergence herbicidal activity, but having primarily post-emergence herbicidal activity, primarily affecting broadleaf vegetation. The present compounds have been found to have particular utility in rice cultivation in selectively affecting the growth of weeds or other undesired vegetation while leaving rice plants substantially unaffected. This invention also relates to a method of controlling undesirable vegetation comprising applying an herbicidally effective amount of a compound as above described to the area or plant locus where control is desired.
• herbicide as used herein, means a compound which controls or modifies the growth of plants.
• herbicideally effective amount is meant an amount of compound which causes a modifying effect upon the growth of plants.
• plants is meant germinant seeds, emerging seedlings and established vegetation, including the roots and above-ground portions.
• modifying effects include all deviations from natural development, for example, killing, retardation, defoliation, desiccation, regulation, stunting, tillering, stimulation, leaf burn, dwarfing, and the like.
• the compounds of the present invention are prepared by reacting a phenoxy aniline having the formula ##SPC2##
• A. Pre-emergence Herbicide Screening Test Using an analytical balance, 20 mg of the compound to be tested is weighed out on a piece of glassine weighing paper. The paper and compound are placed in a 30-ml wide-mouth bottle and 3 ml of acetone containing 1% Tween 20 is added to dissolve the compound. If the material is not soluble in acetone, another solvent such as water, alcohol or dimethylformamide (DMF) is used instead. When DMF is used, only 0.5 ml or less is used to dissolve the compound and then another solvent is used to make the volume up to 3 ml. The 3 ml of solution is sprayed uniformly on the soil contained in a small Styrofoam flat one day after planting weed seeds in the flat or soil. A No. 152 DeVilbiss atomizer is used to apply the spray using compressed air at a pressure of 5 lb/sq. inch.
• DMF dimethylformamide
• the Styrofoam flat which is 7 inches long, 5 inches wide and 2.75 inches deep is filled to a depth of 2 inches with loamy sand soil. Seeds of seven different weed species are planted in individual rows using one species per row across the width of the flat. The seeds are covered with soil so that they are planted at a depth of 0.5 inch.
• the seeds used are hairy crabgrass (Digitaria sanguinalis), yellow foxtail (Setaria glauca), watergrass (Echinochloa crusgalli), red oat (Avena sativa), redroot pigweed (Amaranthus retroflexus), Indian mustard (Brassica juncea) and curly dock (Rumex crispus). Ample seeds are planted to give about 20 to 50 seedlings per row after emergence, depending on the size of the plants.
• the flats are placed in the greenhouse at a temperature of 70° to 85°F and watered by sprinkling.
• the injury rating from 0 to 100% is recorded for each species as percent control with 0% representing no injury and 100% representing complete kill.
• B. Post-emergence Herbicide Screening Test Seeds of six plant species, including hairy crabgrass, watergrass, red oat, mustard, curly dock and pinto beans (Phaseolus vulgaris) are planted in the Styrofoam flats as described above for pre-emergence screening. The flats are placed in the greenhouse at 70° to 85°F and watered daily with a sprinkler. About 10 to 14 days after planting when the primary leaves of the bean plants are almost fully expanded and the first trifoliate leaves are just starting to form, the plants are sprayed. The spray is prepared by weighing out 20 mg of the test compound, dissolving it in 5 ml of acetone containing 1% Tween 20 and then adding 5 ml of water. The solution is sprayed on the foliage using a No. 152 DeVilbiss atomizer at an air pressure of 5 lb/sq. inch.
• Plastic tubs 10 ⁇ 7.5 ⁇ 5.75 inches were filled to a depth of 2 inches with 8 pounds of a loamy sand soil pretreated with 50 ppm Captan 50W and 18. 18. 18 fertilizer.
• One pint of the soil was removed, the remaining soil was leveled and seven rows were impressed across the width of the flat.
• the pint of soil was used to cover 0.5 inches deep the seeds, tubers and part of the cuttings.
• the planted soil was placed in a greenhouse, and irrigated by sprinkling as needed to keep the soil moist.
• Three days after the initial seeding another row was impressed 0.5 inches deep across the width of the flat and seeds of watergrass (Echinochloa crusgalli) were planted and covered by pinching together the soil on either side of the seeder row. Seven to ten days after the original seeding, the soil was flooded with 2 inches of water.
• Test compounds were applied by pipetting into the flood water a stock solution of test compound dissolved in 20 ml of acetone containing 1% Tween 20 at a level proportionate to 2 lb/acre of the test compound. The water level in the tubs was maintained by adding water as needed. Three weeks after application the species were rated visually as percent control from 0 to 100%, where 0% represents no injury and 100% represents complete kill when compared to the untreated check. The rice was substantially unaffected. The percent control was based on the total injury to the other plants.
• the compounds are formulated with an inert carrier, utilizing methods well-known to those skilled in the art, thereby making them suitable for application as dusts, sprays, or drenches and the like, in the form and manner required.
• the mixtures can be dispersed in water with the aid of a wetting agent or they can be employed in organic liquid compositions, oil and water, water in oil emulsions, with or without the addition of wetting, dispersing or emulsifying agents.
• An herbicidally effective amount depends upon the nature of the seeds or plants to be controlled and the rate of application varies from 0.5 to approximately 50 pounds per acre.
• compositions of the present invention are most advantageously applied at the post-emergent, post-flood stage, for example by spraying from either aircraft or with hand-held or other ground level sprayers.
• Incorporation of the compounds into the flood water is most advantageously performed when the rice is at a height of several inches above the water; if applied too early the compounds could cause injury to very young rice plants, if applied much later the compounds would not be as effective against fully-grown weed species.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

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Cited By (11)

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Citations (2)

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• 1975
  • 1975-07-23 US US05/598,486 patent/US3976470A/en not_active Expired - Lifetime
• 1976
  • 1976-06-14 US US05/695,357 patent/US4090865A/en not_active Expired - Lifetime
  • 1976-07-21 RO RO87047A patent/RO81146B/ro unknown
  • 1976-07-23 PL PL1976191393A patent/PL107403B1/pl unknown

Patent Citations (2)

Non-Patent Citations (3)

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